Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D03TGJ
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| Former ID |
DNAP001431
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| Drug Name |
Sorivudine
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| Synonyms |
Usevir (TN)
Click to Show/Hide
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| Drug Type |
Small molecular drug
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| Indication | Virus infection [ICD-11: 1A24-1D9Z] | Approved | [1] | |
| Structure |
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Download2D MOL |
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| Formula |
C11H13BrN2O6
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| Canonical SMILES |
C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CBr
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| InChI |
1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1
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| InChIKey |
GCQYYIHYQMVWLT-HQNLTJAPSA-N
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| CAS Number |
CAS 77181-69-2
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| PubChem Compound ID | ||||
| PubChem Substance ID | ||||
| ChEBI ID |
CHEBI:32152
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| SuperDrug ATC ID |
J05AB15
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides
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|
[2], [3] | |||
| Hierarchy | ||||
| Microbial Enzyme | Dihydropyrimidine dehydrogenase | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Decrease activity; Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by the dihydropyrimidine dehydrogenase of Bacteroides through hydrolysis, which results in the decrease of drug's activity and the increase of the drug's toxicity (lethal toxicity). | |||
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Studied Microbe: Bacteroides eggerthii
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|
[4], [5], [6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Phosphorolytic enzyme | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by the phosphorolytic enzyme of Bacteroides eggerthii through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
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Studied Microbe: Bacteroides fragilis
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|
[4], [5], [6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Phosphorolytic enzyme | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by the phosphorolytic enzyme of Bacteroides fragilis through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
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Studied Microbe: Bacteroides ovatus
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|
[7] | |||
| Hierarchy | ||||
| Resulting Metabolite | Bromovinyluracil | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Sorivudine can be metabolized to Bromovinyluracil by Bacteroides ovatus, which results in the increase of the drug's toxicity. | |||
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Studied Microbe: Bacteroides sp.
Show/Hide Hierarchy
|
[8] | |||
| Hierarchy | ||||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by Bacteroides sp., which results in the increase of the drug's toxicity. | |||
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Studied Microbe: Bacteroides thetaiotaomicron
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|
[7] | |||
| Hierarchy | ||||
| Microbial Enzyme | Phosphorolytic enzyme | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | Bromovinyluracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to Bromovinyluracil by the phosphorolytic enzyme of Bacteroides thetaiotaomicron through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
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Studied Microbe: Bacteroides uniformis
Show/Hide Hierarchy
|
[4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Phosphorolytic enzyme | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by the phosphorolytic enzyme of Bacteroides uniformis through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
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Studied Microbe: Bacteroides vulgatus
Show/Hide Hierarchy
|
[4], [5], [6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Phosphorolytic enzyme | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by the phosphorolytic enzyme of Bacteroides vulgatus through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Klebsiella pneumoniae
Show/Hide Hierarchy
|
[8] | |||
| Hierarchy | ||||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by Klebsiella pneumoniae, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [4] | |||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | (E)-5-(2-bromovinyl)uracil | |||
| Metabolic Effect | Increase toxicity (lethal toxicity) | |||
| Description | Sorivudine can be metabolized to (E)-5-(2-bromovinyl)uracil by gut microbiota through hydrolysis, which results in the increase of the drug's toxicity (lethal toxicity). | |||
| Studied Microbe: Gut microbiota unspecific | [7] | |||
| Metabolic Reaction | N-dealkylation | |||
| Resulting Metabolite | Bromovinyluracil | |||
| Metabolic Effect | Increase toxicity (hepatotoxicity) | |||
| Description | Sorivudine can be metabolized to Bromovinyluracil by gut microbiota through N-dealkylation, which results in the increase of the drug's toxicity (hepatotoxicity). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Human immunodeficiency virus Reverse transcriptase (HIV RT) | Target Info | Modulator | [9], [10] |
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||
| REF 2 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 3 | Gut Pharmacomicrobiomics: the tip of an iceberg of complex interactions between drugs and gut-associated microbes. Gut Pathog. 2012 Nov 30;4(1):16. | |||
| REF 4 | The influence of gut microbiota on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol. 2016;12(1):31-40. | |||
| REF 5 | Gut microbiome interactions with drug metabolism, efficacy, and toxicity. Transl Res. 2017 Jan;179:204-222. | |||
| REF 6 | Gut microbiota modulation of chemotherapy efficacy and toxicity. Nat Rev Gastroenterol Hepatol. 2017 Jun;14(6):356-365. | |||
| REF 7 | Separating host and microbiome contributions to drug pharmacokinetics and toxicity. Science. 2019 Feb 8;363(6427):eaat9931. | |||
| REF 8 | Mechanisms of gastrointestinal microflora on drug metabolism in clinical practice. Saudi Pharm J. 2019 Dec;27(8):1146-1156. | |||
| REF 9 | Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. | |||
| REF 10 | New antivirals with activity against varicella-zoster virus. Ann Neurol. 1994;35 Suppl:S69-72. | |||
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